I didn't mean to imply this
>> why you're assuming people do it so they can seem cool to others I am certain that is not always true. I think often when people are explaining to others some of those people phrase things in a way that is meant to impress others (and somewhat often, impress themselves as well).
My opinions on the "stepping outside comfort zone" discussions are based on my interaction with people. I could, of course, be making incorrect judgements.
Anyway the following is mainly just for me - putting my thoughts into writing lets me think about it a bit more. I am not sure if it helps anyone else. But...
I would not assume people are stating it that way to be cool. I would, based on their other statements, how they behave, the choices they make, the way they treat others... make judgements about the particular individual in question. Those I only know a little bit, I would be more likely to be wrong. I try to make judgement with an understanding of how much uncertainty there is in that judgement.
There really isn't much reason for anyone to place much weight in my thoughts. But I just express what I have seen. And I have seen lots of people talking about "stepping outside your comfort zone" that are misstating what it seems to me is really going on (both from location independent folks and others). This mainly matters when they convince other people what they should be doing.
I think the advice would be better if people said I found out that I didn't like the common expectations and decided to take matters into my own hands to do what I felt would be better for me. And that was a bit scary for me (for most people it is) but I am happy now (or not - I tried something and it didn't work, which is fine, if you don't have this happen you probably are missing out on lots of potentially cool stuff for you). That way people don't go focus on "getting out of their comfort zone" they focus on what would make them happy and then take a look at how to get there even if it means being a bit unconventional.
Then they have to evaluate how willing they are to take risks, or try this new thing in order to achieve that new state. But the focus isn't on being uncomfortable but on getting something they want and whether they are willing to do some things that might be uncomfortable for them to get there.
There are times when just doing something crazy that you are scared to do may make sense. But I think that is fairly rare. Being willing to try something that you are not sure you will like in order to see, makes perfect sense. Accepting that you are willing to risk potential discomfort makes sense.
And there are times to try things you didn't like much (in the past) or you are a bit uncomfortable with because this gives you new data. People are complex. We change over time. What you hated once, you may not hate later. I hated public speaking as a little kid. I figured I could have a job that didn't involve that or working in loud factories (we visited some as a kid and it didn't seem fun to me).
As I grew up one way to make money that on balance appealed to me was giving seminars. Over the years I got past hating public speaking but it still wasn't something I felt at ease with. It did make me uncomfortable. I have done it and am happy. And it still is somewhat uncomfortable. But overall it makes my life better. So avoiding anything not in your comfort zone I think is most often a mistake. But I think it is not so much about doing things outside your comfort zone being innately good (which is how many people talk when they are telling people about their adventures and explaining their path to success...).
I think instead it is about seeking your deep happiness. And not falling into habits that leave you plodding along day to day in a way that isn't how you really want to leave but is easy. And not being limited because you fear any significant step outside your comfort zone. But also mainly it is about getting to places that are in your comfort zone and lead to a life of long term happiness. For many people that is a job in a office that is secure with a spouse and kids and living something close to the 1950s ideal (update in various ways). And for some people it is being a nomad, for others being a farmer for 10 years then a artist, then a computer programmer then, for others being a doctor and spending 3 weeks a year in very poor countries with Doctors without Borders, etc.. For some it is even being a lawyer (even if, in my experience these have a high rate of not being happy in the long term, that isn't universal - some are very happy with that for their entire life).
Each choice has benefits and consequences. I think many people would have happier and more fulfilling lives if they challenged the conventional wisdom (of their situation) much more. I think the main things that are required is examining yourself, think sensibly about the long term, be willing to accept the consequences or your decisions and evaluating how that is working for you.
It isn't so much an overall conventional wisdom that traps people, in my opinion but a more specific conventional wisdom for those you associate with. Like most things, this isn't universal, but it is very common it seems to me. Those you associate with and those you watch, read and listen to will shape what you think is acceptable and what options are sane and what are crazy. Often those limitations are the biggest barrier to you making as much of your life as you can. Occasionally you are blessed to have that pull you forward into being the most you can be. If so, appreciate how lucky you were. I think I was pretty lucky.